Benzarone

Modify Date: 2025-08-25 12:21:07

Benzarone Structure
Benzarone structure
 Common Name Benzarone
CAS Number 1477-19-6 Molecular Weight 266.29100
Density 1.234g/cm3 Boiling Point 473.6ºC at 760mmHg
Molecular Formula C17H14O3 Melting Point 124.3°
MSDS N/A Flash Point 240.2ºC

 Use of Benzarone


Benzarone (Fragivix) is a potent human uric acid transporter 1 (hURAT1) inhibitor, with an IC50 of 2.8 μM in oocyte. Benzarone could lower uric acid serum levels[1].

 Names

Name (2-ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone
Synonym More Synonyms

 Benzarone Biological Activity

Description Benzarone (Fragivix) is a potent human uric acid transporter 1 (hURAT1) inhibitor, with an IC50 of 2.8 μM in oocyte. Benzarone could lower uric acid serum levels[1].
Related Catalog
Target

IC50: 2.8 μM (hURAT1 in oocyte)[1]

References

[1]. Wempe MF, et, al. Developing potent human uric acid transporter 1 (hURAT1) inhibitors. J Med Chem. 2011 Apr 28;54(8):2701-13.

 Chemical & Physical Properties

Density 1.234g/cm3
Boiling Point 473.6ºC at 760mmHg
Melting Point 124.3°
Molecular Formula C17H14O3
Molecular Weight 266.29100
Flash Point 240.2ºC
Exact Mass 266.09400
PSA 50.44000
LogP 3.93180
Vapour Pressure 1.36E-09mmHg at 25°C
Index of Refraction 1.638

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OB2975000
CHEMICAL NAME :
Ketone, 2-ethyl-3-benzofuranyl p-hydroxyphenyl
CAS REGISTRY NUMBER :
1477-19-6
BEILSTEIN REFERENCE NO. :
0222901
LAST UPDATED :
199701
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C17-H14-O3
MOLECULAR WEIGHT :
266.31
WISWESSER LINE NOTATION :
T56 BOJ C2 DOR DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>12 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3400 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>12 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>12 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 154,94,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>12 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52500 mg/kg/5W-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Related to Chronic Data - death
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52500 mg/kg/30W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Nutritional and Gross Metabolic - changes in calcium Related to Chronic Data - death
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,949,1969 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1020 mg/kg
SEX/DURATION :
female 9-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,961,1969
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 9-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,961,1969
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 3,961,1969

 Safety Information

HS Code 2932999099

 Synthetic Route

2-ethylbenzofuran-3-yl p-methoxyphenyl ketone structure

2-ethylbenzofur...

CAS#:3343-80-4

~90%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: J-PHARMA CO., LTD.; WEMPE, Michael, F.; ENDOU, Hitoshi Patent: WO2012/48058 A2, 2012 ; Location in patent: Page/Page column 14-15 ; WO 2012/048058 A2
2-Ethylbenzofuran structure

2-Ethylbenzofuran

CAS#:3131-63-3

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Bulletin de la Societe Chimique de France, , p. 1682,1685
p-Anisoyl chloride structure

p-Anisoyl chloride

CAS#:100-07-2

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Journal of the Chemical Society, , p. 625,627
2-Acetylbenzofuran structure

2-Acetylbenzofuran

CAS#:1646-26-0

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Journal of Medicinal Chemistry, , vol. 54, # 8 p. 2701 - 2713
Salicylaldehyde structure

Salicylaldehyde

CAS#:90-02-8

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Journal of Medicinal Chemistry, , vol. 54, # 8 p. 2701 - 2713
Benzaldehyde structure

Benzaldehyde

CAS#:100-52-7

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: WO2012/48058 A2, ; WO 2012/048058 A2
Methanone, [4-(acetyloxy)phenyl](2-ethyl-3-benzofuranyl) structure

Methanone, [4-(...

CAS#:90908-77-3

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Bulletin de la Societe Chimique de France, , p. 1682,1685
4-Acetoxy-benzoylchloride structure

4-Acetoxy-benzo...

CAS#:27914-73-4

~%

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Bulletin de la Societe Chimique de France, , p. 1682,1685
2-Ethylbenzofuran structure

2-Ethylbenzofuran

CAS#:3131-63-3

4-(benzyloxy)benzoyl chloride structure

4-(benzyloxy)be...

CAS#:1486-50-6

~%

N/A structure

N/A

CAS#:101596-43-4

Benzarone Structure

Benzarone

CAS#:1477-19-6

Literature: Bulletin de la Societe Chimique de France, , p. 1682,1685

 Customs

HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles25

More Articles
Interactions of urate transporter URAT1 in human kidney with uricosuric drugs.

Nephrology (Carlton.) 16(2) , 156-62, (2011)

Hyperuricaemia is a significant factor in a variety of diseases, including gout and cardiovascular diseases. The kidney plays a dominant role in maintaining plasma urate levels through the excretion p...

The EYA tyrosine phosphatase activity is pro-angiogenic and is inhibited by benzbromarone.

PLoS ONE 7(4) , e34806, (2012)

Eyes Absents (EYA) are multifunctional proteins best known for their role in organogenesis. There is accumulating evidence that overexpression of EYAs in breast and ovarian cancers, and in malignant p...

[Effect of benzarone on the oxygen consumption and the mechanical activity of vascular smooth muscle].

Arzneimittelforschung 33(2) , 211-4, (1983)

The influence of 2-ethyl-3-(4-hydroxy-benzoyl)-benzofurane (benzarone, Fragivic) on the energy metabolism of the wall of the rabbit common carotid artery and the rat portal vein was investigated by me...

 Synonyms

(2-Ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone
Fragivix
Benzarone
(2-ETHYL-1-BENZOFURAN-3-YL)(4-HYDROXYPHENYL)METHANONE
Fagivil
Vasoc
Fragivil
Benzaron
Venagil
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